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alcohol with a strong acid
oxonium


alcohol with a strong base
alkoxide


alcohol with Tosic acid (or TsX)
alkyl tosylate (R-OTs)


alcohol with HCl, PCl3, or SOCl2
alkyl chloride


alcohol with HBr or PBr3
alkyl bromide


alcohol with HI or PI3
alkyl iodide


alcohol with H2SO4 or TsOH
alkene


primary alcohol with PCC
aldehyde


secondary alcohol with PCC
ketone


primary alcohol with jones
carboxylic acid


secondary alcohol with jones
ketone


alkane with Br and light
alkyl bromide (with Br on most subst. carbon)


alkene with mCPBA
epoxide


alkene with O3, Zn, and H2O
ketone and aldehyde


alkene with KMnO3 (cold, dilute)
diol


alkene with KMnO3 (hot, concentrated)
ketone and carboxylic acid
